2-Propenenitrile, 3-hydroxy- → 3-(2,3-Dichlorophenacylamino)acrylonitrile

HRID 247626

Reaction equation

HRID 247626 reaction equation
Cl.[Cl:2][C:3]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5](=[O:8])[CH2:6][NH2:7].O[CH:15]=[CH:16][C:17]#[N:18].[Na]>C(O)C>[Cl:2][C:3]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5](=[O:8])[CH2:6][NH:7][CH:15]=[CH:16][C:17]#[N:18]

Participants

5

Reactant 3

HCID 30540732-Propenenitrile, 3-hydroxy-HCID 5360545SodiumHCID 22151845Ethanone, 2-amino-1-(2,3-dichlorophenyl)-, hydrochloride

Product 1

HCID 679440943-(2,3-Dichlorophenacylamino)acrylonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 g of 2,3-dichlorophenacylamine hydrochloride, 1 g of 3-hydroxyacrylonitrile, sodium salt, and 20 ml of ethanol are heated for 2 hours under reflux. The reaction mixture is concentrated by evaporation and the oily residue is purified by column chromatography (silica gel; elution with a 4:1 mixture of toluene/ethyl acetate), affording 3-(2,3-dichlorophenacylamino)acrylonitrile in the cis/trans ratio of 5:1. Melting point: 122°-125° C.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture is concentrated by evaporation
  3. customthe oily residue is purified by column chromatography (silica gel
  4. washelution
  5. additionwith a 4:1 mixture of toluene/ethyl acetate),

Sources & evidence

ORD record
ord-1a3d972cbc9a4d70b4175f9bd46bf6ef
Source dataset
uspto-grants-1987_11
Patent number
US04709053

Linked notes

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